1,1'-Carbonyldiimidazole → 3-(3-ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3-methylphthalimido)propionamide
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:17]2[C:21](=[O:22])[C:20]3=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:28])[CH2:13][C:14](O)=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:42][OH:43]>O1CCCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:17]2[C:21](=[O:22])[C:20]3=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:28])[CH2:13][C:14]([NH:42][OH:43])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]Participants
Procedure
3-(3-Ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3-methylphthalimido)propionamide was prepared by the procedure of Example 1 from 3-(3-ethoxy-4-methoxyphenyl)-3-(3-methylphthalimido)propanoic acid (1.50 g, 3.91 mmol), carbonyldiimidazole (698 mg, 4.30 mmol) and hydroxylamine hydrochloride (330 mg, 4.75 mmol) in tetrahydrofuran (5 mL) to afford 3-(3-ethoxy-4-methoxyphenyl)-N-hydroxy-3-(3-methylphthalimido)propionamide as a white solid (1.4 g, 90% yield): mp, 165.0-166.5° C.; 1H NMR (DMSO-d6) δ1.32 (t, J=6.9 Hz, 3H, CH3), 2.61 (s, 3H, CH3), 3.10 (d, J=7.9 Hz, 2H, CH2), 3.72 (s, 3H, CH3), 3.98 (q, J=7.0 Hz, 2H, CH2), 5.66 (t, J=7.8 Hz, 1H, NCH), 6.87-6.90 (m, 2H, Ar), 7.02 (br s, 1H, Ar), 7.57-7.69 (m, 3H, Ar), 8.80 (br s, 1H, OH), 10.59 (br s, 1H, NH); 13C NMR (DMSO-d6) δ14.71, 16.99, 34.21, 49.95, 55.45, 63.73, 111.72, 112.38, 119.70, 120.76, 127.79, 131.27, 131.67, 134.06, 136.66, 137.29, 147.65, 148.51, 166.06, 167.55, 168.31; Anal Calcd for C21H22N2O6+H2O: C, 60.57; H, 5.81; N, 6.73. Found: C, 60.83; H, 5.72; N, 6.53.
Sources & evidence
- ORD record
- ord-71303503984742128b2d7b231225f705
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06656964B2
Reaction notes
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